


The Singer and the Detective

by Happyfeet2002



Category: Chicago PD (TV), alternate universe Famous singer Hailey Upton
Genre: Alternate Universe, Country & Western
Language: English
Status: In-Progress
Published: 2021-02-28
Updated: 2021-03-02
Packaged: 2021-03-19 06:47:41
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 2
Words: 3,899
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/29746590
Author URL: https://archiveofourown.org/users/Happyfeet2002/pseuds/Happyfeet2002
Summary: In an alternate universe Hailey Upton is a famous singer, who grew up in Texas, and Jay Halstead happens to be transferring to a precinct in Texas leaving his life and brother behind in Chicago. What happens when these two different people meet? Find out in this Upstead Fanfic
Comments: 1
Kudos: 20





	1. Chapter 1

Part 1 (Meeting her) 

Jay Halstead was transferred to another District, this time Texas. He didn’t expect life to change so quickly, one second in Chicago the next second on a flight to Texas. 

Jay finally got to sleep and 20 minutes later he jerked awake, opening his eyes due to the captain making an announcement: “All right folks we are landing in Dallas Texas in five minutes, make sure your seatbelts are on, and stay in your seats until we land.” 

The captain stopped talking and Jay checked his phone: 3 missed calls from Will Halstead

Sighing he switched his phone to Cellular data. 

“Hey sorry just landed.” He said.

“I know I am sorry, I didn’t mean to scare you.” He said. “Alright. I will call you again once I get settled.” 

Jay didn’t particularly like this move to Texas, but he had no other choice. It was either this or New York and being in the same city with His ex didn’t strike him as suitable. 

Since the 21st district got overrun by Kelton, everyone split up, he hadn’t talked to anyone from the unit in six months. They all had been separated. 

Getting up from his seat. He reached for his luggage up top. Once his luggage was secure in his grip he started moving, shuffling through the people as he made his way off the plane. 

Goodness he could already feel the weather change stepping off the plane. “This is gonna be great.” Jay sighed under his breath. 

He decided to ask someone where the coffee is, because after all of this, coffee sounds great. 

“Hey do you know any places to get good coffee at?” He asked one of the flight attendants following him out of the door leading to the open space in the DFW airport.

“Umm...yes there is a Starbucks, just turn through that hall. “You see that Barnes and Noble.” She asked him pointing, and he nodded. “It is right next to it.” She said. 

“Thank you.” Jay said as he smiled at her and started walking towards the Barnes and Noble. 

He thought it was cool how thick their accents were as he met more and more people. 

He had heard Texas accents on tv but never met someone with a thick accent like everyone in this airport.

Sitting down sipping his coffee, he checked his phone again. A photo from iPhone memories popped up with Kevin, Him and Adam all laughing. 

The sudden realization hit him, leaving the home that he knew as his forever home.

It was too late now, but would he go back if he could, honestly he didn’t know, but right now this was probably the best place he could be right now. 

After his coffee was finished, he decided to explore a bit in the airport more before heading to the new precinct. 

He decided on looking in the souvenirs in the gift shop. Will loved to collect souvenirs from different states, and Jay wanted to get him something, because obviously he wasn’t here himself. 

After looking through a bunch of different ones, he decided on the little glass globe, but instead of snow, it was just water. 

He carried it up to the desk to ring it up. “Not from here huh.” The cashier said. “What threw you off.” He asked her smiling. 

“The hoody you have on, let me give you a tip, you should know it’s almost always hot here.” “The days we get rain, it’s glorious for everyone.” 

She said as handed her his credit card. “Thanks.” he said unzipping his hoody revealing his old Intelligence tee. 

After he finished buying the globe in the store, he finally decided that he was done exploring and that it was time to get settled in at his new desk at his new district. 

Turning the corner he collided with someone. 

“Oh, my gosh, I’m so sorry.” The small figure said. Jay could hear the thick Texas accent. 

“I have to hide.” She said. 

“What why?” He questioned putting his hand on her shoulder. 

“I’m a cop, are you in trouble.” He said helping the jumpy blonde to her feet. 

No,not at all.” She smiled. Wow she had a beautiful smile he thought to himself. “I need to hide somehow ,they are coming.” She said. 

Immediately he took off his jacket and put it over her shoulders, and put his arm around her putting his Chicago hat on her head. 

She leaned into his chest as he put his arms around her, pretending that he was her boyfriend. 

He switched sides with her so she was hidden against the wall. She looked above his shoulder waiting as the paparazzi passed bye. 

“Thanks I owe you.” She said. “Here’s your hat back.” He took the hat from her. “Not at all, I’m a cop, well detective...” “I’m an expert at being secretive.” “Oh, is that right.” She smiled at him. 

They stayed like this for a few minutes before she brought herself back to reality. “Umm..anyways thanks again.” “I really gotta get goin.” She said leaning off the wall. 

“Oh, do you want your Jacket back.” She said. “No, you keep it, in case paparazzi comes by again.” He smiled at her. “It looks better on you anyways.” Smiling she started to walk off out the doors headed in Jay’s opposite direction. 

“Wait, what was your name.” He said raising his voice as she ran farther away. She turned around stopping.

“Guess you’ll have to find out detective.” She said smirking and running off again. “My names Jay..Jay Halstead.” He said hoping she would give her name. 

“Well Detective Halstead, I am sure you will figure it out.” She said smiling once more before biting her lip and running off again.

Jay knew he shouldn’t be already flirting getting a fresh new start and all, but there was something about her that he absolutely admired. His mood changed since he met her. 

He wondered why paparazzi would be after her. Could she have been famous? A singer? A celebrity? He didn’t know, but he promised he would find out. 

Authors note:  
Thank you to whoever read this!!  
I am so excited to continue this story, I wonder where it will go. Stay tuned for chapter two!!


	2. Getting settled /Meeting her again

**Summary for the Chapter:**

> In an alternate universe Hailey Upton is a famous singer, who grew up in Texas, and Jay Halstead happens to be transferring to a precinct in Texas leaving his life and brother behind in Chicago. What happens when these two different people meet? Find out in this Upstead Fanfic

After meeting her three days ago,Jay had a hard time focusing on why he really moved to Texas. 

He put an alarm for five in the morning so he could get up and out early for his move as a detective in Texas. He had no idea what it would be like except for the fact that they like guns here, way more than they did in Chicago.   
Hopefully it would be smooth sailing. Groggily hitting his alarm he sat up in bed, after a while heading to the kitchen in the small apartment to make some coffee. 

After getting some caffeine into his system.  
, he took an Uber to see if he could buy a car, getting out of the Uber, he thanked him and started looking at some cars.

After looking for a while he met a dealer and got a great deal for a Truck that was basically new.

He signed the papers which took a while, but he was happy he got a good car, mind that a truck which he would only drive in Chicago, nothing else. He got to the new district in Dallas. 

Turning the ignition off he slowly hopped out of his truck and took in the new look, the new people, and the new air which quickly got humid again. “So this will be fun.”  
He hummed to himself walking up the precinct steps. It looked so different from the 21st.He walked into the doors and was immediately greeted by a desk sergeant, “Hi can I help you.” She said.

“Uh..yes I just got transferred yesterday from the 21st in Chicago.”

“Oh, you must be Jay Halstead.” She said looking at him. “Yes that I am.” I said, mad that I used that choice of words. 

She chuckled dryly and said I could go to my new desk. 

Like what I was used to the bullpen was up two flights of stairs but this bullpen was on the left side instead of the right.  
I walked slowly opening the door. 

Faces looked up from their desks as I walked in. Friendly smiles mostly. They probably all knew who I was. 

“Alright, so we will keep this introduction short and sweet.” A tall women said.

“Meet your new seargent Jay Halstead.” “Umm...did you just say Seargent.” I said slowly standing up. “Yes, you are from Chicago right. Jay nodded . 

“Hank Voight told us that you were promoted after he retired.” Jay did not know this. 

Jay watched her walk out as he turned to the detectives left in the room.

“Umm..okay how do I start..umm let’s see, Hi everybody it’s nice to meet new detectives, I do not have a speech prepared because I had no idea I was your seargent until now.” 

Everyone chuckled at his remark. As he relaxed a little and started meeting everyone. 

After a few hours of getting settled and meeting everyone he asked one of the detectives who had one of the desks up front.

“Alright Detective Martin, where are we at with this Kidnapping case.” He said as she looked up.

“Umm right.” She stood up from her desk walking to the bulletin board up front. 

“Kyle ridgewater.” Last seen Monday, he is a five year old boy, and his father has many priors for abuse to the mother and him.” She finished saying.

“Alright, I want someone on phone records of who the dad might have contacted, and I need someone to find where this mother lives.” 

“The people who do not have anything I want you guys to go through the dads social media, find hidden emails...” he trailed off.After making sure they knew what they were doing, he sat at his desk for a while.

“Does anybody know where your last seargent’s office was.” He said as he looked around seeing if anybody knew.

“Yeah he was in that back room.” Martin said. Pointing her finger towards the back. “Thanks.” He said as he started to walk towards the room.

It was definitely smaller than Voights office, and he could already tell that this District ran a whole lot different than Voight ran his unit. 

After placing his PC on the desk he finished setting everything else up.“Sarge.” Detective Adams said.

“We got a lead on the dad.” He said as Jay got up from his desk. “Alright , what do we have.” Jay asked crossing his arms.

“The dad was seen at a local grocery store with a stolen car. As seen here.” He said as he played a video watching the dad get out of the car and shutting it.” 

“We ran the plates, and it belongs to a Rosa Samson.” Another detective added. “Do we know who this Rosa Samson is.” Jay asked him. 

“Yeah, she works at a gas station, she has no priors, our guess is that she is a random person that he decided to take a car from.” “Alright let’s hit it.” Jay said. 

He was thinking he was slowly becoming Voight, even if it was just for a day. Voight always said that when they would find a stash house or anything like that. 

Hailey Uptons POV

Sitting in my dressing room, I slowly strummed my guitar, as I thought of a tune. A knock on the door interrupted my thoughts.

“Yes.” I said “you are live in five Hailey.” The voice said. It was Amanda her Manager.

“Alright I’ll be out in a few.” I said back not wanting to interrupt my flow of tunes that were just pouring out of my head. “Don’t disappear like last time.” Amanda said. 

Hailey looked down at the floor, and just nodded her head to herself getting back to her thoughts. 

Hailey only dissapeared last time she had to do a concert was because right before the concert her dad had a heart attack that night.

She couldn’t bare to go on stage and pretend everything was fine, when it clearly was not in her head. 

She felt bad that she had let down her fans, but she did not want to have another panic attack on stage in front of thousands of people. 

Setting her guitar down she quickly finished up her makeup. 

She looked in the mirror one last time before picking her guitar back up and strapping it over her shoulder, and walked out of the dressing room. 

After the concert her phone buzzed. Hailey it’s your father.” 

I know you don’t want to see him, but he wants to see you.

The text read it was from her mom. 

She scoffed at this and just stared at her phone for a while. I will try my best to get over there as soon as I can.

She replied slamming her phone on the makeup table. The truth is Hailey did not want to go see her father, he didn’t deserve it.

All of her memories from the age five up until now, he never put good memories in her head. She didn’t know what caused the drinking but he started doing it more and more as she grew up. 

She could barely defend herself, she was glad her two brothers survived. 

Of course her father stopped drinking eventually but what really stuck out was that her mom stayed with him the entire time, even though he abused her too, and Hailey was mad at her mom for this. 

Hailey tried to sleep that night but couldn’t, and she was just tossing and turning until she decided to strum her guitar for some comfort. 

Her aunt gave her the first guitar that she ever had when she was eight years old. 

She took a like to it, and practiced all of her free time on it. After her aunt died when she was 14 years old. 

she made a song dedicated to her. That song made her famous, and since then she has been one of the most famous artists in Dallas Texas. 

For the next twenty minutes she wrote down good material, potentially for her next song that she would release of her producer liked it.

After sitting there admiring her new lyrics she made a last second choice to find a bar that was open late at night.

Of course this bar was the one that she played at, when she had free time, without her manager or any of her bodyguards knowing. 

She stepped onto the small stage through the curtains after hearing her name being announced. 

After we got a confession, and rescued the little girl. It was a while before she got back to her real family, due to them being hours away. 

It all played out, but some of the officers almost got shot. It was a trap and I feel like it was my fault that it was poorly planned out. 

It turns out the kidnapper was waiting for us and found out we were on his trail, and there was a huge shootout. 

No one really could have known but, I feel that there was something else I could have done. 

After sitting at the office finishing some more of the paperwork, I decided to take the tradition that I had in Chicago when I went to Molly’s after all of the cases, to find a bar and make it a tradition again. 

After seemingly looking around town for a while. I finally found a bar that was open and looked decent enough to go inside. 

Walking inside there was big crowd of people inside the bar, stared not even for a second and got back to drinking. 

After putting my keys into my pocket I ordered a scotch on the rocks. I sat there for a bit looking around until a noise from the speakers sounded “Please welcome Hailey Upton.”The speakers said and a blonde girl popped out from the curtains. 

Jay watched as the blonde sat down and situated herself. Recognizing her immediately from the airport he watched her sing for a while. 

Amazed that this was probably why that there was paparazzi following her. 

She looked at the crowd smiling. “The next one is dedicated to my aunt. I wrote this while I was grieving, because she was my best friend.” She said clearing her throat. 

Jay felt sentiment for this stranger that he just met at the airport just a couple of days ago.

Her voice began to fill the bar with sweet sound. “You can see how I how used to play, not in a serious way.” “You taught me, how to strum and now I can.” 

“Because you are my guardian angel, and something tells me, that you. Oh..you can still see and watch over me.”

Jay watched as she switched her fingers on all of the different chords and sang softly on the mic. 

After she finished she thanked the crowd, and slowly stepped down off the stage. 

Quickly asking for a drink, Jay noticed her was staring at her and turned fast toward his drink on the stool. He noticed that she took a seat next to him. “Hey, I still have your jacket.” She nudged him smiling, which made him turn his head towards her.

“I know I gave it to you Hailey.” Jay felt good finally to know her name. 

“It’s really comfy, I slept in it actually.” 

She said. Jay’s expression on his face changed to surprise, and then led to a smirk. “This is going to sound so strange...” “you know what never mind.” She quickly stopped herself looking at the ground. 

He studied her for a second before talking.

“Just speaking from truth here...I have heard a lot of weird things...try me.” He suggested. “Okay fine...uh...”She smirked.

“My brother had the same jacket as you, he actually left it to me before he uh..” she trailed off not finishing her sentence and just taking a drink of her beer in front of her. 

“So that’s uh why I like it, it reminds me a lot of Jackson.” She cleared her throat trying not to cry.

“Oh..I’m sorry..I didn’t mean for you to...” He said changing his tone of voice. “No not at all..he’s not dead..uh he just..we haven’t seen him in months.”  
She said looking up at him.

“MIA?” Jay asked her. “Uh..we don’t know..his whole team just seemed to go missing after a few months..we tried for a while to track them down....after a while there was nothing else we could really do.” She said. 

Jay noticed by the tone of her voice that she was done talking about it. “I’m sorry.” He offered.

She nodded in thanks not saying a word for a few seconds. 

“Umm..anyways I will be in some of the worst trouble if my manager catches me here.” She said gathering her stuff. “I have a truck...and it’s late at night, and I’m going to assume since you snuck out that you walked here.”

“If your asking me if I need a ride...I think I’ll be okay, it’s only a few minutes away.” She said smiling at him, then slinging her guitar over her chest.

“But..thank you for the offer.” She said making her way out the door.

“Hailey... I know we don’t know each other...but please the least I could do is drive you home.” Jay pleaded.

“Your not going to try and kill me are you.” She chuckled. “I promise I will not kill you.” 

“Pinky promise, come on that’s a trust no one can break.” Jay said holding out his pinky.

“Woah..the pinky, yes I trust you.” She said laughing.

Jay laughed at her laughing. She stopped and her cheeks turned red.

“Alright..shall we.” He said holding out his arm leading her out the door. 

“We shall.” She strolling out. Jay was glad she was trusting him, the last thing he wanted to do is make her feel not safe.

On the drive there he decided to make light conversation. 

“So did you grow up or move here.” He said.

She looked at him for a second.“I was born here. Texas has always been my home.” She said. 

Jay smiled at this because he loved how sentimental she was.

“What about you, obviously you have no accent, so where are you from?”

She questioned him looking down and strumming her guitar. “Uh..I transferred from an intelligence unit in Chicago, to a different one here.” Jay said keeping one hand on the steering wheel. 

“I know that I seemed short earlier about my older brother being missing and all..” She started but Jay stopped her.

“Not at all, I’m sorry for telling you to talk about it.” “If it helps at all, I did a couple of tours in Afghanistan..”

“I just really miss him..he was my best friend after my Aunt died.” Jay let her talk. “he was my shoulder to cry on, the person I would go to for guidance in highschool.” 

“Gosh...I was..I am so close to him.” She said carefully changing her words. 

“I’m so sorry Hailey.” He said deciding whether or not he should put his hand on top of hers or do something for comfort but decided against it when she started talking again.

“This is me right here.” She said as Jay slowed down and stopped in front of a semi-big house.

“Umm..thank you so much for the ride.” She said hopping out of his giant truck.

He smiled a little bit at how she had to use the step to get down. 

Quickly changed it when she looked at him. “Of course, anytime, and I mean anytime, here’s my card.”   
Oh he wishes he hadn’t did that,but his hand was already offering the small rectangular card to her.

“Thanks I will.” She said. “Wow.” She said.

“Umm....I’m glad you like the card he said playfully.” “Actually thank you, it was nice to talk to someone other than the people who barely listen.”

She said. “Anyways, I’ll see you around.”

“If you can make it, but I am sure you will be busy, I have a concert Next Friday.” Ask for Kayla Dean and she will know.” 

She offered before shutting the truck door. 

He rolled down his window. “I will most definitely try.” He said partially yelling before she looked at him like he was crazy.

“Sorry.” He whispered.

She just laughed as she walked up the steps. 

Jay was falling in love again, how could this be possible, it has only been a couple of days. She must be worth he thought to himself, he made sure she got in safely making sure she walked through her door, then put the truck in drive, and he did not stop thinking about her when he got back to his apartment , but he was able to finally catch some shut eye after a while.


End file.
